PREPARATION OF 6-FLUOROBENZISOTHIAZOLES VIA A REGIOSELECTIVE NUCLEOPHILIC AROMATIC-SUBSTITUTION REACTION

被引:15
作者
FINK, DM
STRUPCZEWSKI, JT
机构
[1] Chemical Research Department, Neuroscience Strategic Business Unit, Hoechst-Roussel Pharmaceuticals Inc., Somerville, NJ 08876
关键词
D O I
10.1016/0040-4039(93)88095-Z
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient three step procedure for the preparation of 6-fluoro- 1,2-benzisothiazoles is described. The key step is a regioselective nucleophilic aromatic substitution reaction in which the carbonyl group of a ketone or aldehyde directs nucleophilic displacement to the ortho position in preference to the para position.
引用
收藏
页码:6525 / 6528
页数:4
相关论文
共 9 条
[1]   THE ORTHO-PARA RATIO IN ACTIVATION OF AROMATIC NUCLEOPHILIC SUBSTITUTION BY THE NITRO GROUP [J].
BUNNETT, JF ;
MORATH, RJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1955, 77 (19) :5051-5055
[3]  
Davis M., 1972, ADV HETEROCYCLIC CHE, V14, P43
[4]   DERIVATIVES OF SULFENIC ACIDS .43. CHLORINOLYSIS OF CERTAIN ARYL BENZYL SULFIDES AS A ROUTE TO SULFENYL CHLORIDES [J].
KHARASCH, N ;
LANGFORD, RB .
JOURNAL OF ORGANIC CHEMISTRY, 1963, 28 (07) :1903-&
[5]  
KUHLE E, 1971, SYNTH-INT J METHODS, P617
[6]  
LAROCK RC, 1989, COMPREHENSIVE ORGANI, P587
[7]  
MARKERT J, 1982, LIEBIGS ANN CHEM, P768
[8]  
STRUPCZEWSKI JT, 1990, 200TH AM CHEM SOC M
[9]  
1982, Patent No. 4350691